Isosilychristin - Compound Card

Isosilychristin

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Isosilychristin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Lignan
    • Subclass: Flavonolignan
Canonical Smiles OCC1c2c(ccc(c2OC1c1ccc(c(c1)OC)O)O)C1Oc2cc(O)cc(c2C(=O)C1O)O
InChI InChI=1S/C25H22O10/c1-33-17-6-10(2-4-14(17)28)23-13(9-26)19-12(3-5-15(29)25(19)35-23)24-22(32)21(31)20-16(30)7-11(27)8-18(20)34-24/h2-8,13,22-24,26-30,32H,9H2,1H3
InChIKey QYCJAWYDGRZSTO-UHFFFAOYSA-N
Formula C25H22O10
HBA 10
HBD 6
MW 482.44
Rotatable Bonds 4
TPSA 166.14
LogP 2.4
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 482.12
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Silybum marianum Asteraceae Plantae 92921

Showing of synonyms

  • AbouZid S.F, Ahmed H.S, et al. (2017). Chemotaxonomic and biosynthetic relationships between flavonolignans produced by Silybum marianum populations. Fitoterapia, 2017, 119, 175-184. [View] [PubMed]
Pubchem: 14849116
Chebi: 176166
Nmrshiftdb2: 70073623
CPRiL: 416097
Structure

SMILES: c1ccccc1C(C2)Oc(c23)cccc3C(CC4=O)Oc(c45)cccc5

Level: 2

Mol. Weight: 482.44 g/mol

Structure

SMILES: C1COc(c12)cccc2C(CC3=O)Oc(c34)cccc4

Level: 1

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1cccc(c12)OC(C2)c3ccccc3

Level: 1

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 482.44 g/mol

Structure

SMILES: C1COc(c12)cccc2

Level: 0

Mol. Weight: 482.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 482.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.65
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.3
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
52.85
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.68
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.82
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-498.94
Rat (Acute)
2.45
Rat (Chronic Oral)
3.61
Fathead Minnow
5.21
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
581.85
Hydration Free Energy
-3.15
Log(D) at pH=7.4
2.36
Log(P)
1.57
Log S
-5.86
Log(Vapor Pressure)
-9.17
Melting Point
221.09
pKa Acid
5.84
pKa Basic
3.63
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9048
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8894
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8757
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8684
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8655
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8627
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8504
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8271
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8231
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8040
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8037
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.8030
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8021
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8002
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7962
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7950
Major strawberry allergen Fra a 1-3 D0E0C7 FRA13_FRAAN Fragaria ananassa 4 0.7878
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7867
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7816
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7799
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7716
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7703
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7635
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7633
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7596
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7596
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7542
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7506
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7487
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7473
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7454
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7429
Annexin A5 P08758 ANXA5_HUMAN Homo sapiens 3 0.7401
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7383
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7348
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7328
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7273
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7248
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7225
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7218
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7162
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7139
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7135
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7130
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7129
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7051
Protease Q5RTL1 Q5RTL1_9HIV1 Human immunodeficiency virus 1 4 0.7041
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7019
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7016

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